


Pretty Little Thing

by outoftheashes



Series: Breaking The Rules [2]
Category: Supernatural
Genre: Anal Fingering, Bottom Dean, Dean in Panties, Dom Sam, Dom Sam Winchester, Feminization, M/M, Orgasm Denial, Panties, Rimming, Rimming Kink, Season/Series 04, Sub Dean, Sub Dean Winchester, feminization kink
Language: English
Status: Completed
Published: 2016-07-21
Updated: 2016-07-21
Packaged: 2018-07-25 18:32:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,442
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7543435
Author URL: https://archiveofourown.org/users/outoftheashes/pseuds/outoftheashes
Summary: <blockquote class="userstuff">
              <p>The noises Sam coaxes from him… he’s not sure how to feel about them.</p>
            </blockquote>





	Pretty Little Thing

**Author's Note:**

> Written for SPN Kink Bingo  
> Square Filled: Feminization 
> 
> I'm also on tumblr! URL is samanddeaninpanties
> 
> Reading part 1 is not required in order to understand this fic. At the end of the day it's a simple pwp.

“Freak.”

Sam always eats Dean's ass until he's so fucking sensitive he can't stop himself from trying to squirm away from the contact.

Now is no different. He doesn't respond to Dean's comment with words, just keeps fucking his tongue in and out of Dean's hole.

“Dude, c-c'mon --” Dean chokes, unable to speak for a moment as he tries to hold back a whimper. The noises Sam coaxes from him... he's not sure how to feel about them. “Don't you wanna come?”

Finally, _finally,_ Sam pulls away, licking his god damned lips (lips that should be fucking illegal in every state).

“Oh, I plan on it. But here's the thing – I've got patience and lots of it. And I kinda feel like drawing this out all day long.”

They are between cases, so Dean believes this threat wholeheartedly.

“O-okay... but. Can you at least fuck me?”

“Think I'm gonna wait since you've got such a hard on for calling me names.”

“ _What_? Sam, that's just. Fucking torture, that's what it is. You're sick, man.” He pauses a moment before adding, “At least lemme see your dick.”

“Nah.”

Sam smirks and _gets off the bed._ That little shit.

“Where are you --”

“Stay right there,” Sam demands, grabbing the keys to baby. There's wicked promises in his eyes that make Dean's breath hitch.

“This is such bullshit!”

“Complaining isn't gonna get you your way, big brother. Might as well sit back and enjoy what's coming next.”

And just like fucking that Sam's out the door, leaving Dean naked and vulnerable in their shitty ass motel room with nothing but his thoughts for company.

 

* * *

 

All alone.

He's all alone awkwardly laying on the frumpy mattress, the smell of sex and sweat, _his_ sweat permeating the air – just because Sammy told him to.

Throughout this whole Twilight Zone experience, Sam has remained eerily calm. Dean puts up a front, yeah, but the reality of it is he's been inwardly freaking out ever since they started doing... whatever the fuck it is that they're doing.

They haven't been together long, a little over a week and Sam has only rimmed Dean silly. He never takes off his clothes. Dean's seen more of Sam's skin before they were together (fucking girls mere feet away from each other, in the dark, always in the dark, but Dean could still _see_ him at least) than he ever does now.

Why won't Sam let Dean touch him, too? Is it a kinky thing? Is he not into Dean _that_ way?

Whatever the reason... it doesn't seem fair.

 

* * *

 

 

It takes Sam a god damned hour to return and the younger Winchester is practically vibrating. Giddy even. And he's gotta admit it's kind of adorable.

At least it is until he remembers Sammy has _plans_ and Dean's not entirely sure if he'll find them sexy or not.

“Took you long enough!” Ugh, Dean Winchester is _not whining._

Christ.

Sam raises a brow and plops down a reusable shopping bag (god, Sam is _such_ a nerd and Dean loves it) on the bed.

“Have a look.”

“This better be good...”

“The fuck?!” Dean yelps when he sees what Sammy bought – a fucking checkered red skirt, knee high stocking type things and fucking red silky panties. “You've gotta be shittin' me.”

“You wanted to get me off, right?” Sam asks, eyes dark.

“Well, yeah --”

“This'll do it.” Sam leans in close, mouth brushing Dean's ear. Dean's pulse quickens. “Be my big sister a few hours. Think you can do that?”

 _Fuck._ He's in big trouble.

“Jesus Christ, you are one kinky son of a bitch.”

“You don't know the half of it. So...”

“Fuck it. _Fine._ ” He snatches up the bag and runs for the bathroom before Sam can do something crazy like insist he should be the one to put all this crap on Dean himself.

 

* * *

 

 

The satiny, lace-y whatever-the-fuck kind of panties Sammy got him are a bitch to pull up his legs, are far too fucking tight for his liking around his cock and balls and Dean hates them.

Okay, maybe hate is a strong word. Maybe he finds them kinda hot. He _did_ do something similar once upon a time for Rhonda, after all.

Just. Not quite this intense.

The internet gives Dean tips on how to create a 'smokey eye' and for some reason, he thinks he can pull it off. Four unintentional smudges and eight fucking pokes in the eye later Dean gives up and hopes he hasn't failed and this'll be enough to appease his weird ass brother.

On the bright side he's 85% sure he doesn't look like a clown, so at least Sammy won't run away screaming in terror.

He takes a few deep breathes and forces himself to open the door, eyes scanning the tiny motel room for Sam and – Sam's already on him, possessive hands exploring him, groping his ass.

“Fuck you're a pretty thing. Mine. My big sister, my girl --”

“S-Saaaaam,” Dean gasps and his fucking cock is rock hard in seconds.

Apparently, Sam isn't the only kinky one in the family.

The _look_ in Sam's eyes as he pushes him against the nearest wall – he wants to destroy Dean.

It shouldn't be hot, it really shouldn't.

Sam's pressing against his asshole through the thin fabric of the panties and Dean moans like a whore. He picks Dean up like he weighs nothing and Dean doesn't think twice – he wraps his legs around his little brother's waist.

“Wet and eager, sweet sister,” Sam remarks, sounding calm even though his mouth and hands are all over Dean, owning him. “Knew you would be.”

“Christ, Sammy. Please. F-fuck m-me -”

He's too turned on to be annoyed by the smug look on Sam's face. How is it that _Sam_ knew what Dean had been completely oblivious about?

Sam laughs softly before pressing his fingers against Dean's mouth. “Open.”

He complies, taking what his brother is so intent on giving him, running his tongue between Sam's thick fingers.

Sam yanks his fingers free and it's Dean's turn to feel smug because Sam looks _undone,_ more undone than Dean even.

Not for long though because his little brother yanks his panties aside hard enough he's surprised the fabric isn't torn to shreds and slicks his fingers up with lube he'd kept in his pocket – his Sammy had come prepared.

Looks like Dean is gonna get fucked after all, yes yes yes.

“Oh _fuck_ , pretty little thing... you. Opened yourself up for me,” Sam breathes after dipping two fingers inside and feeling how fucking loose Dean is.

Dean had made use of his alone time while Sam had gone off to the store and is really fucking pleased with Sam's reaction.

“Yup.”

Sam clears his throat and regains his composure. “When did I give you permission to touch your slutty hole, hmm?”

“You didn't.”

“Yeah, that's what I thought.” A pause. “No cock for you then.”

“Dude! You can't punish me when it's _your_ fault for not clarifying what you wanted,” Dean points out. Fuck, fuck, he's so hard and he's gonna lose his shit if he doesn't feel Sammy's cock in his ass, pronto.

“Nice try, sweetheart. But I've made up my mind.”

Sam continues to fingerfuck Dean's asshole until there's four fingers crammed inside, massaging his sweet spot over and over again, his free hand fiddling with the fabric of Dean's skirt.

“What exactly are you try'na do here?” Dean asks, thighs trembling.

“Make my pretty little thing sorry,” Sam replies as if it's the most obvious thing in the world. “Are you? Are you sorry, sweet sister?”

He needs Sammy to stop.

No.

He needs more, needs him to keep going. Needs to be stretched so fucking wide he's feeling it for days. Needs Sam to fill the empty places inside of him.

“Yes,” the word spills out of him automatically. “Very.”

“Good.” Sam hums in approval and palms Dean's ass. “Do you feel pretty? Do you feel like my pretty, pretty princess?”

“G-god yes.”

Dammit, when did Sammy get such a dirty mouth?

“Mm. If that's true then we gotta show everyone just how pretty and slutty you are.”

“O-okay. Whatever you say, Sammy.” Dean tries his best to fuck himself on Sam's fingers because the fucker is teasing him, purposely missing his prostate.

“Right now.”

Sam pulls his fingers free, leaving Dean's ass sore and used, dick throbbing, so fucking wet with pre-come and lowers Dean to the ground.

It's not until Sam grabs all their shit and leaves the motel room that Dean finally straightens his skirt and follows him on shaky legs.

 


End file.
